This case involves the complicated vaginal delivery of a male born prematurely at 34 weeks gestation. The mother was diagnosed with maternal diabetes and pregnancy induced hypertension and during a prenatal visit, her doctor told her that the baby may be too large and need to be delivered via a C-section to prevent any complication. Upon admission on the day of delivery, a bedside sonogram revealed that the fetus was in a cephalic presentation and that there was normal fetal movement but no reports of shoulder dystocia were mentioned. The parents mentioned the previous claims by doctors that shoulder dystocia may be a problem but the physician on call told them not to worry. The on-call physician elected to proceed with a natural delivery and unfortunately ran into several complications with a delivery that lasted several hours. As a result of the difficult delivery, the infant suffered from neurological injuries including the inability to use his right arm, and brain injuries due to hypoxia including severe cognitive and developmental delays.